p-Toluenesulfonic acid monohydrate → HCID 22262203, compound

HRID 1610674Notes

Reaction equation

HRID 1610674 reaction equation
[Br:1][C:2]1[C:7]2[CH:8](O)[CH2:9][CH2:10][CH2:11][C:12]([CH3:14])([CH3:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:7]2[CH:8]=[CH:9][CH2:10][CH2:11][C:12]([CH3:14])([CH3:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22262105HCID 22262105, compound

Product 1

HCID 22262203HCID 22262203, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-bromo-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ol (4.402 g, 16.35 mmol) and p-toluenesulfonic acid monohydrate (0.31 g, 1.64 mmol) in toluene (80 ml) was heated under reflux in a reaction vessel equipped with a Dean-Stark trap under dehydrating conditions for 0.5 hr. After the reaction solution was cooled to room temperature, the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane) to give the objective substance.

Workup

  1. temperatureunder reflux in a reaction vessel
  2. customequipped with a Dean-Stark trap under dehydrating conditions for 0.5 hr
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained crude product
  5. customwas purified by silica gel column chromatography (hexane)
  6. customto give the objective substance

Sources & evidence

ORD record
ord-e9bdd53c23434bbaad67e83afdae99a7
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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